The broad, long-term objectives of this proposal are to develop new highly enantioselective methods for the formation of carbon-carbon bonds. Mechanistic studies are employed to streamline the development of these methods and to probe the catalyst structure and reactivity. A central theme of this research is the enantioselective generation of chiral quaternary centers through asymmetric addition of alkyl, vinyl, allyl, phenyl, and alkynyl groups to ketones. Although many catalysts will promote the addition of such groups to aldehydes with high enantioselectivity, these catalysts do not promote the analogous additions to ketones. We have developed catalytic systems to address these important ketone addition reactions, allowing easy access to a variety of enantioenriched tertiary alcohols. [unreadable] [unreadable] The Specific Aims of this proposal are: I. Development of a Catalytic Asymmetric Synthesis of Chiral Tertiary Alcohols and II. Development of a Practical Catalytic Asymmetric Synthesis of Homoallylic Alcohols. [unreadable] [unreadable] This project presents new methods to synthesize important chiral building blocks that were not previously accessible, but find utility in health-related applications, particularly in the synthesis of chiral pharmaceutical agents. [unreadable] [unreadable]